


Wanna Bet?

by EmeraldWaves



Series: Pour Me A Drink [1]
Category: Haikyuu!!
Genre: 1920s AU, Alcohol, Gambling, M/M, Smoking, bottom!iwa, minor side kurotsuki, porn with minor plot, speakeasy au
Language: English
Status: Completed
Published: 2018-08-08
Updated: 2018-08-08
Packaged: 2019-06-24 02:26:58
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,715
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15620466
Author URL: https://archiveofourown.org/users/EmeraldWaves/pseuds/EmeraldWaves
Summary: Iwaizumi Hajime is stressed. His job has been eating away at his life and his best friend Kuroo decides he could use a drink. The only problem: prohibition. Kuroo takes Iwaizumi to the very illegal underground speakeasy, and there he meets the most beautiful and obnoxious man he's ever encountered.





	Wanna Bet?

**Author's Note:**

> This fic was born from the prompt "Wanna bet?" while playing a game with some friends!

The sound of dice hitting the padded tables and the smell of smoke overtook Hajime's senses the moment he walked into the damn place. Mumbles and murmurs filled the room, laughter bursting through the cacophony of sounds in the shockingly large space.

This wasn't really Hajime's scene.

Kuroo's hand rest on his shoulder. "Enjoy yourself, Iwaizumi," he said, his voice a soft purr.

"Right," Hajime replied, adjusting his tie against his neck. Already he felt sweaty and hot. Patrons seemed to float about the floor, clinking glasses, the rowdy movement of drunken bodies.

"Take your hat off, loosen your tie, _enjoy_. You don't have to worry about getting caught," Kuroo said, flicking a finger against Hajime's hat before placing a cigarette between his own lips. "Tsukki and I are going to play at the blackjack table. Get a drink and join us." The blond nodded silently, agreeing with his messy haired lover.

"Sure," Hajime said.

Kuroo wrapped his arm around the blond's waist and pulled him into the crowd of people, leaving Hajime to stand on his own, glancing out over the scene in front of him.

Actually, a cigarette didn't seem like a bad idea. He pulled one from the small box in his pocket and immediately lit it, taking a long drag. He wasn't normally so uptight, but something about the atmosphere in the large speakeasy put him on edge.

He'd begun to wander, his feet dragging across the floor. He moved the cigarette up and down with his teeth, the ash on the tip falling to the ground carelessly. His brow was furrowed as he watched the drunken bar patrons flit about foolishly.

It had been years since his lips had touched alcohol; prohibition had made it rather difficult to procure any sort of alcoholic beverage. Hajime was never much of a drinker, so the laws really hadn't affected him much, but lately, with the stress at work, he found himself missing the satisfying liquid.

Perhaps Kuroo had sensed that within him when he'd pulled him aside after hours one evening.

"C'mon out this Friday," he said. "I know a place."

For some reason, the invitation hadn't surprised Hajime. He'd agreed when Kuroo had explained his best friend, a man named Bokuto Koutarou owned the place. Tucked away underneath a bookshop, there were shelves which opened up to stairs which led deep underground, away from watchful eyes.

So, here he stood, in the middle of the crowded speakeasy, searching for... something? Now he was here, he wasn't certain if a drink appealed to him. Instead, he wandered, watching people squander their money, laughing as drinks sloshed onto the floor. Men kissed women, women hung over other women, and men had their arms slung around other men... The scene was addicting to watch and though Hajime didn't quite know how to participate, he couldn't take his eyes off it.

"Wanna bet?" A playful voice caught Hajime's ear at the blackjack table next to him. A handsome young man smirked at him, dark framed glasses sat upon his face, but his brown eyes glowed under the dim lighting. His finger trailed over the edge of the deck of the cards, flipping them down onto the table. The flap of the shuffle caught Hajime's eye, but it didn't stay focused for long, especially when the man smiled even more. He was _handsome_ and Hajime was certain this man was well aware of his attractiveness.

"Bet?" Hajime said, hating how idiotic he sounded. He knew what the man meant.

The trill of the cards hit his ear again, and his eyes watched as the man's fingers shuffled once more.

He hadn't come here to gamble, but then again he wasn't sure why he had come here at all.

The man's table was empty, which surprised Hajime. He was attractive, clearly talented with his hands, he had _appeal_. Maybe his table was rigged. At a place like this, Hajime wouldn't have been surprised.

Still, Hajime found himself taking a seat at the table. "Alright. I'm in," he said, placing cash on the table to trade for chips. 

"Good." The man smiled, pushing the chips across the table slowly, his fingers brushing over Hajime's. "I was hoping you would be."

"Why me?" Hajime asked, raising his eyebrow. He stamped his cigarette out in the ashtray in front of him. He gripped his palm over the top of his hat, placing it and his jacket on the empty seat next to him. There wasn't anything particularly lavish about his outfit; he didn't look like a man with money.

"Mm," the man hummed. "You looked like you're due for a good time. What's your name?" He began to shuffle, his fingers curling them as he flipped the cards against one another.

"Tch," he scoffed. "A good time giving all my money to you? I can only assume that's why your table is empty."

The man placed his hand on his chest, gasping dramatically. "I am offended you think I would try and cheat you out of money."

"Heh. At a place like this? Isn't that the point?," Hajime said, tempted to take out another cigarette.

"You didn't answer my question," the man said, avoiding Hajime's comment.

"You didn't answer mine," Hajime retorted.

The man pouted, his cheeks puffing out. "Mine was a lot simpler."

Sighing, Hajime rolled his eyes. This man... somehow an invisible force pulled Hajime towards him, like a siren calling him towards the dangerous, invisible rocks, about to bleed him dry. And yet, he couldn't resist. "Iwaizumi Hajime," he said, remembering the man had asked his name.

"I see!" he purred, leaning forward as he placed two cards in front of him, face up. A 2 and 7. Low, and not a good starting hand. Hajime immediately frowned. "Oof," the dealer smirked. "Not off to a good start. I assume you wanna hit?"

"Yeah." Hajime pulled out his cigarette after all, lighting it. "Hit me."

"Gladly," the man purred. He was pretty. Far too pretty for his own good.

He flipped another card over. An 8. "Tough spot," the dealer sighed. Hajime took a long drag on his cigarette, rubbing his forehead. 17. Not a great number to have. He needed a 4 or lower to stay under 21 and the odds of that happening were not great, especially when he was the only one sitting at the table.

"What do you wanna do, Iwa?" The man's brown eyes narrowed, his finger gently pulling on the cards.

Hajime rest his elbow on the side of the table with a huff, letting his cheek fall against his fist. "I dunno, you're the dealer, give me some... sage advice."

"Now, now, Iwa," he winked. "You know I can't do that. I play for the house, and the house wouldn't be very happy if I helped them lose money."

He rolled his eyes, partially at the nickname the man seemed to have adopted, but also for his damn response. Idiot. Hajime was a complete idiot. His money was going out the window.

"And what exactly is your name, dealer?" he hissed. If this man was going to give him a nickname, Hajime was allowed to do the same.

"Oikawa Tooru," he winked again. "But you can call me Tooru if you want."

"Okay, Shittykawa, fuck it," he said, flicking the ash into the tray. "Hit me."

Oikawa's brow furrowed. "Not with that attitude I won't."

Hajime narrowed his eyes. "You won't? I thought you 'played for the house'," he grinned. "Odds are I'm gonna to lose."

Oikawa ran his finger over the edge of the card, a smirk pulling across his lips. "You're not wrong," he said leaning forward. "Are you sure you want to take such a _risk_?" He held out the last word, letting his tongue click at the end of his breath.

"Why not," Hajime shrugged. "I resigned myself to losing money the second I sat down at your table." He pulled the cigarette to his lips, taking one final drag from the shrunken butt before slamming it down into the ashtray, crushing it. "Hell, if I win I'll buy us both a drink."

The dealer blinked, his palm coming up to his face as Oikawa cupped his own cheek. "Oh Iwa! I'm not supposed to accept drinks from patrons, but I suppose I could make an exception for you." Picking up the card, Oikawa held it between his thumb and pointer finger, facing it towards the table so neither could see it. "And here I hold your fate between my fingertips," he mused.

What a dramatic man. Hajime pursed his lips, rolling his eyes. "Just flip it."

Oikawa waggled his finger back and forth. "How impatient!" he teased, but flipped the card anyway, layering it over the others in front a Hajime.

The 4 of hearts glared up at Hajime and he swallowed. A 4.

21.

"Blackjack," Oikawa purred. "Looks like someone owes me a drink."

Hajime blinked, letting a huff of air escape his lips. "Well look at that. Guess I do." He smirked leaning back in the chair.

"Yachi!" Oikawa called out.

Within moments, a small blonde girl bounded up to the table. Her blonde hair bobbed against her cheek, her smiling pulling wide. "Hi Tooru! What can I do for you?"

"Get us two drinks," he said. "Akaashi knows what I like, and..." he glanced to Hajime, waiting for him to give his drink order.

"Ah... just a whiskey on the rocks is fine," he said.

"Tooru," she giggled, "you're not supposed to drink on the job." Her voice was teasing, but Oikawa shrugged nonchalantly.

"It's a celebratory beverage, for me and my new friend Iwa!" he explained.

"Oh," she smiled. "Well, nice to meet you Iwa! I guess it can be our secret for now," she winked. "But you owe me!" Waving, she walked off to retrieve their drinks.

"Do you wanna play again?" Oikawa asked, scooping up the cards in front of him, shuffling them into the deck. His fingers moved against the cards rapidly and Hajime watched with curious eyes, unable to pull his gaze from the movement.

Oikawa nodded his head to Yachi when she placed their drinks down. Oikawa's was something red, though Hajime couldn't place it. Instead he raised his own glass to his lips, swallowing the burning liquid down.

"So," Oikawa repeated, "how 'bout it?"

"I dunno," Hajime chuckled. "This is how it always goes right?"

Oikawa tilted his head at the question. "Whatever do you mean, Iwa?"

"You let me win the first few so I think I'm on a streak and then eventually I keep betting it all until I lose everything I earned and more," he explained.

Raising an eyebrow, Oikawa popped out his hip. "Seems you caught me."

"Isn't that highly unethical?" he asked, swirling the drink in his hand, the ice clinking sharply against the glass.

Oikawa glanced around the speakeasy. "And what exactly about this place screams ethical to you?" he chuckled. "You're so funny, Iwa!" He took a large swig of the red drink, practically downing it in one go. "You don't have to play if you don't want. In fact, there are... plenty of other things we can do here," he grinned, leaning forward again. His brown eyes glistened with a hint of playfulness Hajime had seen glimpses of all throughout the night, and he felt his heartbeat quicken.

Tilting his drink back, he downed the small shot of whiskey left in the glass. "Alright then," he smirked, slamming the glass onto the table. "Show me."

~~

Oikawa's lips caressed Hajime's neck, and the sound that left his own mouth was ungodly. His voice hitched in his throat, his head pressing against the wall. Oikawa's hands explored up his shirt, pulling at the top of Hajime's pants.

"Oi-Oikawa..." he stammered. "This is..."

"A backroom," he said, his fingers touching over Hajime's toned abs. "They're meant to be used for this purpose. Patrons can rent them, but since I work here..." he trailed off, helping Hajime remove his tie.

"I get in for free..." Hajime panted.

"Aren't you lucky, Iwa?" he chuckled, sucking on his neck.

"Oikawa..." he moaned softly, his hands sliding up his back, burying them in his brown sweeping hair. He hadn't meant for things to go in this direction, but he should've known once Oikawa's brown eyes had caught his own. The twinkle which had sparked in his eyes should've been an obvious clue. Then he had laced their fingers together and immediately brought him through a door near the back of the speakeasy.

Hajime hadn't expected the tucked away bar to have private rooms for such devious activities, but now he was here with Oikawa's hands and lips touching his body and he sure as hell wasn't going to complain.

Oikawa made fast work of Hajime's clothes, running his finger down is chest, forcing every button of his shirt to come undone. "Mmm," he chuckled, moving his hand up Hajime's bare chest. "You're so strong, Iwa," he purred, leaning against him. "Can I touch you all over?"

And really, how could Hajime deny him? It was the gamble he took coming back here with Oikawa, and one he was completely ready to commit to.

"Yes..." he sighed, moaning when Oikawa's lips wrapped around one of his nipples, his body trembling. He didn't mind succumbing to the touch, Oikawa's wet lips suckling on his skin. "Dammit..." he hissed, gripping his hair. "O-Oikawa."

Letting go with a pop, drool trickled down Oikawa's chin as he smirked, looking up at Hajime. "Has no one kissed you here before?"

Hajime shook his head, his cheeks flushing redder than they had been before. Looking down at Oikawa's face, his lips swollen and red, Hajime couldn't help it. Dammit, he was far too attractive for his own good. Hajime was completely trapped in the pleasure, the feeling of his lips on his skin.

"Has anyone ever kissed you before?!" he gasped and rose up. His lithe fingers caressed Hajime's chin, his lips hovering just above Hajime's own.

Hajime rolled his eyes. "I'm not a virgin, if that's what you're askin'," he snorted.

"Oh good, I was about to feel bad if your first time was with little ol' me..." he hummed and planted a kiss on Hajime lips. He ran his fingers down his chest, dropping to the floor as his fingers curled around the button on his pants. "Now I get to have some fun," he purred, licking his lips.

Hajime watched Oikawa as if he was moving in slow motion, every touch, every action tantalizing slow. Oikawa pulled down Hajime's pants, releasing his hardened cock. "Mmm... Good. I'm glad you're hard already," Oikawa smirked, licking his lips.

He wrapped them around the head of Hajime's cock, suckling on the tip. The slurping noises were lewd and loud, and his swollen lips curled perfectly around the straining head.

"Dammit..." Hajime moaned, his head pressing back against the wall. He rolled his hips up, desperate to thrust into Oikawa's warm mouth, but Oikawa's hands pressed against his hips, pinning him to the wall. A whine left his mouth. This man was truly evil, just as Hajime had suspected. He should've known the moment he sat down at the table, he would succumb to the wiles of this man.

Oikawa moved his lips down Hajime's shaft, his tongue rolling against the base. Hajime's legs trembled, his hips jerking now Oikawa had let go. He groaned and panted, his breath growing louder and louder. "Oikawa..."

He hummed around Hajime's cock and released it with a pop. "Should I get you nice and ready?" he smirked, reaching for the lube stored away in the drawer next to the door.

"Just... do it..." he growled, curling his hand into a fist, gripping Oikawa's hair.

"How needy Iwa," he purred, flicking his tongue over the pre-cum bubbling at Hajime's tip.

With the buzz of alcohol and pleasure shooting up Hajime's spine, he rolled his back against the wall, sighing when Oikawa returned his mouth to his cock. He bobbed his head faster, gently stroking his hands up Hajime's thighs as he snaked his hand around, pressing a lubed up finger to his entrance.

Hajime lurched forward, his body shaking at the penetration, but damn Oikawa's fingers felt good. He thrust his finger inside of Hajime, moving in time with his mouth. He was damn good at this, and Hajime was convinced this was the best blow job he'd ever received.

Oikawa's tongue rolled against the length of his shaft and Hajime sucked in air sharply when he added a second finger. "D-Damn..." he moaned, spreading his legs even more to make room. He wanted to thrust down against the fingers, but he wanted to push forward into Oikawa's mouth. The hand in his brown hair squeezed tight, grunting at the feeling.

"Mmm," Oikawa hummed, swirling his tongue over the tip. "You taste so good Iwa," he smirked, pushing his fingers up even deeper, searching for the spot he knew Iwa would love.

"Ngh!" he grunted, biting down on his lip. His ass clenched around Oikawa's fingers, tightening when he pushed over his prostate.

"There we go," he purred. "You're getting so nice and loose."

"C'mon Shittykawa, just do it."

He frowned, staring up at Hajime as he pressed a third finger inside, stretching him even more. "This is your punishment for that mean line, Iwa," he pouted, though his eyes sparkled deviously. Hajime could tell the idiot was loving this.

"H-Hah... Thanks... feels good," he grunted, watching Oikawa thrust frantically up into him. He scissored his fingers, stretching him wide, before pulling out, reaching over to grab a condom.

Smirking, his stood up, letting his own pants drop to the floor as he rolled the condom over his dripping length. Leaning forward, he tugged on Hajime's earlobe. "It'll feel even better when it's my cock inside of you," he purred.

"O-Oikawa..." he breathed, the anticipation making his cock twitch with excitement.

Cheeks flushing, Hajime wrapped his arms around Oikawa's neck. The dealer's hands scooped under his ass and hoisted him up, wrapping his legs around Oikawa's waist. Smoothly, in a rapid motion, Oikawa thrust his cock inside.

"NGH!" Hajime yelped, letting his head press against the wall. His ankles hooked around Oikawa's waist, and his naked back lay against the wall, his hips rolling down towards the pleasurable stretch.

"Mmm you take it so well Iwa," Oikawa muttered, his lips kissing at Hajime's chest. His tongue ran across his clavicle, sending shivers straight to his ass.

"Fuckin' move," he growled, pressing his fingers into Oikawa's back, his hips rolling forward.

"How demanding!" Oikawa chuckled, pressing their lips together as he pulled his hips down only to snap back up.

Hajime immediately felt dizzy. He kept his hands on his back, digging his nails directly into Oikawa's pulsing muscles. With each thrust, he felt his back push against the wall, Oikawa pounding up into him. His cock was thick, stretching Hajime wide, and it'd been so long since he'd felt this way.

He panted, his mouth hanging open. Everything about his being was drowning in Oikawa, his touch, his kisses, his hot breath trailing over his bare, sweaty skin. "S-Shit..." he groaned.

"I know," Oikawa moaned, pressing his lips against Hajime's neck, sucking gently at the tight skin. "You're so tight, Iwa... Ngh... sucking me up in you..."

Hajime thrust his hips down, his own cock slapping against his stomach as he tried to meet Oikawa's thrusts. He squeezed his ass, especially every time Oikawa would hit against his prostate. Everything was so sensitive, his body tingled, so close to an edge he hadn't reached in forever.

His body felt loose and open, free, and all stress had floated from his mind as he took in Oikawa's scent, and let his body feel it. His heels pressed against Oikawa's ass, his back slipping up the wall.

"You're clenching, Iwa," Oikawa teased softly, his own breath hitching in his throat. "You're making it difficult for me to hold on."

"Oh?" he smirked, his cheeks bright red as he stared down at Oikawa. He'd been so lost in himself, the tightness and pleasure rocketing through his body, he hadn't noticed how affected Oikawa was.

Sweat rolled down the side of his face, his cheeks were red, his mouth parted as breath huffed through his lips. Suddenly, Hajime could feel the way Oikawa's hands trembled against his ass.

He smirked. All this time he'd been affecting Oikawa just as much as Oikawa had been affecting him. "You can finish if you can't hold back," he teased, panting heavily, his chest heaving.

"Only... if you cum with me," Oikawa smirked, licking his lips. He wrapped a hand around Hajime's throbbing cock and began to stroke it as fast as he thrust.

"A-Ah!" Hajime gasped, bouncing with the movement. He tried to keep his legs locked, but his body was slowly deteriorating into jello. "T-Tooru..." he gasped. "I-I can't!" Grunting, he pressed his head against the wall as his hips twitched up against Oikawa's hand. "I'm cumming..." He spurt out, his cock making a mess over his chest. "F-Fuck..." he groaned, his chest rising and falling intensely as he gasped for air.

Clenching his ass hard was enough to bring Oikawa to his finish too. With a few frantic thrusts, his breath hit Hajime's neck in spurts, before he buried his cock completely inside, pouring the finish into the condom. "Damn..." he whimpered, rubbing his nose against his skin. "You called me Tooru."

Hajime blushed. Of all the things the damn idiot could say...

"Yeah well... you were being... amazing or whatever," he grumbled, letting his fingers trail through Oikawa's brown locks.

"Heh... I win it seems," Oikawa smirked, slowly lowering Hajime to the ground once he pulled out of him.

"You win?" Hajime frowned, twisting his lips. "I believe I won Blackjack earlier."

"Hm..." Oikawa hummed, leaning towards Hajime. He pressed their foreheads together, and kissed him, tugging gently on his lip. "I guess we're tied then. You'll just have to come and see me again... for a tiebreaker of course."

Hajime smiled, nipping playfully at Oikawa's lip. "Maybe I will."

**Author's Note:**

> I had a lot of fun writing this fic, a speakeasy AU is something I've been dying to do! Thanks to adriana for betaing and turning this into a whole series!! You can read [Adriana's](https://archiveofourown.org/users/xladysaya) Kurotsuki fic [here](https://archiveofourown.org/works/15620604)! And we might do more who knows (I know I really wanna do a BokuAka prequel where they open the bar etc). I'm SO HONORED to finally be doing a collab with Adri!!! (it only took us years) She is one of my favorite people and so incredibly talented, just.. an amazing writer!! <3 I love her so so much and this made me so happy so I hope it is enjoyable for everyone! ANYWAY Thank you for reading!
> 
> [emeraldwaves](http://emeraldwaves.tumblr.com/) is my tumblr where I take requests  
> [musickazoo](https://twitter.com/musickazoo) is my twitter!


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